tert-butyl 1H-pyrrole-3-carboxylate → tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]pyrrole-3-carboxylate

HRID 1821931Notes

Reaction equation

HRID 1821931 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC[CH:15]([CH2:32]C([O-])=O)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=1>CS(C)=O.[Na+].[Cl-]>[C:1]([O:5][C:6]([C:8]1[CH:12]=[CH:11][N:10]([CH2:32][CH:15]([O:7][C:6](=[O:5])[CH3:8])[CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:23]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11171190tert-butyl 1H-pyrrole-3-carboxylateHCID 86606004HCID 86606004, compound

Product 1

HCID 12992899tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]pyrrole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
110 °C

Procedure

0.145 g (0.867 mmol) tert-butylpyrrole-3-carboxylate is dissolved in 10 ml absolute DMSO, mixed with 0.107 g (0.952 mmol) potassium-tert-butylate and stirred at 110° C. for 15 min. A solution of 0.333 g (0.864 mmol) [1-bromo-3-(4-octylphenoxy)propan-2-yl]acetate in 10 ml absolute DMSO is added drop-wise. Following 30 minutes of heating at 110° C. and subsequent cooling, hydrolysis is carried out in saturated NaCl solution. Four extractions with diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps using saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellow oil which is purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 93:7) and yields the product as a colorless oil.

Workup

  1. waitFollowing 30 minutes
  2. temperatureof heating at 110° C.
  3. customsubsequent cooling, hydrolysis
  4. extractionFour extractions
  5. concentrationwith diethyl ether, combination of the organic phases, concentration to half the volume
  6. customon the rotary evaporator, three
  7. washwash steps
  8. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  9. customleave as a crude product a yellow oil which
  10. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 93:7)

Sources & evidence

ORD record
ord-d5e7f4581a5e48b1b6896c2f9f1c4a42
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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